Tiffany and Jesse

How We Met

I, Tiffany, worked at a bank as a teller and every couple of days Jesse would come in with a deposit for the local pizza shop. (He was the manager there at the time.) We were able to small chat at each visit and soon, I learned that Jesse likes to collect old and rare money. I started to put aside the “fancy” money I found for him and while doing do, also became interested in starting my own collection. Months went by and Tiffany was now curious. She asked another employee from the pizza shop if Jesse was available and word got out. Soon, the two began chatting online and learned that they had a mutual friend and lots of common interests. More months went by and they finally went on their first day-date: A trip to a local farm to play with baby goats!

Tiffany and Jesse's Engagement in Portland, ME

Jesse and Tiffany have been inseparable ever since. Together, they make an incredible team and they can’t wait to see what the future holds for them. #TeamJessany

How He Asked

I, Tiffany, deliver food part time and Wednesday nights are usually quite busy. I got an order and noticed that I’d be delivering to my close friend John! I got really excited and zipped over there with his order as fast as I could. He greeted me at the apartment entrance and said to come up to his room since his money is upstairs. Normally, I don’t do that and I’d wait at the entrance, but I had never seen John’s place before. He showed me the living room and said “I’ll go get the cash. Check out the sweet view I have from the balcony!” I crossed the living room and opened the big door to find Jesse on one knee with a little ring in a blue box. He said a few words that I honestly can’t remember… I was still so stunned to see him there. We exchanged kisses and I realized that 2dinein (the amazing food delivery company I work for) was totally in on it! The dispatcher and my boss had been messaging Jesse to let him know where I was and when I’d get there. Turns out, the food I brought was for us! I had just delivered my own dinner to my own engagement!! 2dinein paid for our meal and gave me the rest of the night off to enjoy the beautiful evening with my handsome man. It was awesome, totally unexpected and it played out perfectly!

Where to Propose in Portland, ME

Special Thanks

Jordan Tallman
Photographer